#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024472.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024472
loop_
_publ_author_name
'Michael Harmata'
'Kanok-on Rayanil'
'Vinson R. Espejo'
'Charles L. Barnes'
_publ_section_title
;
Benzothiazines in Synthesis. Further Studies of the Intramolecular,
Stereoselective Addition of Sulfonimidoyl Carbanions to α,β-Unsaturated
Functional Groups
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3214
_journal_page_last               3216
_journal_paper_doi               10.1021/jo900151d
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C22 H19 N O2 S'
_chemical_formula_weight         361.44
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1614(5)
_cell_length_b                   12.3551(7)
_cell_length_c                   17.7310(11)
_cell_measurement_reflns_used    6740
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.3
_cell_volume                     1787.90(19)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12824
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         2.01
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0391P)²+0.2581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0773
_reflns_number_gt                3589
_reflns_number_total             3945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900151d_si_001.cif
_cod_data_source_block           VE-i-119
_cod_database_code               4024472
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.54134(5) -0.00758(3) 0.10261(2) 0.03127(10) Uani 1 1 d . . .
O1 O 0.56503(17) -0.06124(10) 0.17427(7) 0.0463(3) Uani 1 1 d . . .
O2 O 0.70990(16) 0.23855(9) 0.26026(7) 0.0428(3) Uani 1 1 d . . .
N1 N 0.37467(17) -0.00809(12) 0.06345(9) 0.0412(3) Uani 1 1 d . . .
C1 C 0.59977(19) 0.12989(11) 0.11298(9) 0.0275(3) Uani 1 1 d . . .
H1A H 0.7048 0.1354 0.1407 0.033 Uiso 1 1 calc R . .
H1B H 0.6129 0.1645 0.0630 0.033 Uiso 1 1 calc R . .
C2 C 0.4610(2) 0.18491(12) 0.15778(8) 0.0268(3) Uani 1 1 d . . .
H2 H 0.4493 0.1466 0.2072 0.032 Uiso 1 1 calc R . .
C3 C 0.29941(19) 0.17449(12) 0.11496(8) 0.0282(3) Uani 1 1 d . . .
C4 C 0.1792(2) 0.25463(13) 0.11808(10) 0.0342(4) Uani 1 1 d . . .
H4 H 0.1993 0.3180 0.1470 0.041 Uiso 1 1 calc R . .
C5 C 0.0306(2) 0.24460(15) 0.08004(10) 0.0391(4) Uani 1 1 d . . .
H5 H -0.0498 0.3000 0.0835 0.047 Uiso 1 1 calc R . .
C6 C 0.0018(2) 0.15295(16) 0.03718(10) 0.0400(4) Uani 1 1 d . . .
H6 H -0.0982 0.1458 0.0102 0.048 Uiso 1 1 calc R . .
C7 C 0.1180(2) 0.07198(15) 0.03359(10) 0.0396(4) Uani 1 1 d . . .
H7 H 0.0963 0.0091 0.0044 0.048 Uiso 1 1 calc R . .
C8 C 0.2671(2) 0.08064(13) 0.07199(9) 0.0320(3) Uani 1 1 d . . .
C9 C 0.6776(2) -0.06892(12) 0.03769(9) 0.0305(3) Uani 1 1 d . . .
C10 C 0.7974(2) -0.13776(13) 0.06536(10) 0.0394(4) Uani 1 1 d . . .
H10 H 0.8091 -0.1490 0.1181 0.047 Uiso 1 1 calc R . .
C11 C 0.8997(3) -0.18987(15) 0.01465(12) 0.0485(5) Uani 1 1 d . . .
H11 H 0.9812 -0.2383 0.0327 0.058 Uiso 1 1 calc R . .
C12 C 0.8844(2) -0.17211(15) -0.06166(11) 0.0462(5) Uani 1 1 d . . .
H12 H 0.9539 -0.2091 -0.0960 0.055 Uiso 1 1 calc R . .
C13 C 0.7675(2) -0.10023(14) -0.08848(10) 0.0426(4) Uani 1 1 d . . .
H13 H 0.7599 -0.0862 -0.1410 0.051 Uiso 1 1 calc R . .
C14 C 0.6620(2) -0.04889(14) -0.03895(9) 0.0366(4) Uani 1 1 d . . .
H14 H 0.5803 -0.0008 -0.0571 0.044 Uiso 1 1 calc R . .
C15 C 0.5104(2) 0.30232(12) 0.17362(9) 0.0303(3) Uani 1 1 d . . .
H15A H 0.5282 0.3399 0.1250 0.036 Uiso 1 1 calc R . .
H15B H 0.4189 0.3391 0.1998 0.036 Uiso 1 1 calc R . .
C16 C 0.6631(2) 0.31292(13) 0.22094(9) 0.0310(3) Uani 1 1 d . . .
C17 C 0.7550(2) 0.41751(13) 0.21905(9) 0.0314(3) Uani 1 1 d . . .
C18 C 0.8918(3) 0.42983(17) 0.26434(12) 0.0553(6) Uani 1 1 d . . .
H18 H 0.9245 0.3723 0.2966 0.066 Uiso 1 1 calc R . .
C19 C 0.9810(3) 0.52438(19) 0.26325(14) 0.0655(6) Uani 1 1 d . . .
H19 H 1.0745 0.5313 0.2948 0.079 Uiso 1 1 calc R . .
C20 C 0.9373(3) 0.60813(17) 0.21766(12) 0.0547(6) Uani 1 1 d . . .
H20 H 1.0004 0.6727 0.2167 0.066 Uiso 1 1 calc R . .
C21 C 0.8010(3) 0.59785(18) 0.17316(13) 0.0637(6) Uani 1 1 d . . .
H21 H 0.7686 0.6561 0.1415 0.076 Uiso 1 1 calc R . .
C22 C 0.7101(2) 0.50336(17) 0.17389(11) 0.0501(5) Uani 1 1 d . . .
H22 H 0.6155 0.4976 0.1429 0.060 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 121.11(9) . . ?
O1 S1 C9 106.91(8) . . ?
N1 S1 C9 105.18(8) . . ?
O1 S1 C1 108.18(8) . . ?
N1 S1 C1 106.89(8) . . ?
C9 S1 C1 107.97(7) . . ?
C8 N1 S1 120.11(12) . . ?
C2 C1 S1 106.16(10) . . ?
C2 C1 H1A 110.5 . . ?
S1 C1 H1A 110.5 . . ?
C2 C1 H1B 110.5 . . ?
S1 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C3 C2 C15 113.48(12) . . ?
C3 C2 C1 109.95(12) . . ?
C15 C2 C1 108.60(13) . . ?
C3 C2 H2 108.2 . . ?
C15 C2 H2 108.2 . . ?
C1 C2 H2 108.2 . . ?
C4 C3 C8 118.21(15) . . ?
C4 C3 C2 121.86(13) . . ?
C8 C3 C2 119.92(14) . . ?
C5 C4 C3 121.99(16) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C6 C5 C4 119.14(16) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 120.08(16) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 121.35(16) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C3 119.22(16) . . ?
C7 C8 N1 115.42(15) . . ?
C3 C8 N1 125.36(15) . . ?
C10 C9 C14 121.40(15) . . ?
C10 C9 S1 118.40(13) . . ?
C14 C9 S1 120.19(13) . . ?
C9 C10 C11 118.73(17) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 120.58(18) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.11(17) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.25(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 118.87(16) . . ?
C13 C14 H14 120.6 . . ?
C9 C14 H14 120.6 . . ?
C16 C15 C2 113.69(13) . . ?
C16 C15 H15A 108.8 . . ?
C2 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C2 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O2 C16 C17 120.57(15) . . ?
O2 C16 C15 120.91(15) . . ?
C17 C16 C15 118.52(14) . . ?
C22 C17 C18 117.86(17) . . ?
C22 C17 C16 122.99(15) . . ?
C18 C17 C16 119.15(16) . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 121.0(2) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 118.99(19) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C20 C21 C22 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 120.78(19) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4461(12) . ?
S1 N1 1.5272(15) . ?
S1 C9 1.7708(16) . ?
S1 C1 1.7736(14) . ?
O2 C16 1.2151(19) . ?
N1 C8 1.413(2) . ?
C1 C2 1.541(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.527(2) . ?
C2 C15 1.532(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.395(2) . ?
C3 C8 1.412(2) . ?
C4 C5 1.393(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.398(2) . ?
C7 H7 0.9500 . ?
C9 C10 1.386(2) . ?
C9 C14 1.387(2) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.508(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.495(2) . ?
C17 C22 1.379(3) . ?
C17 C18 1.384(2) . ?
C18 C19 1.377(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.361(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.370(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C8 96.62(15) . . . . ?
C9 S1 N1 C8 -142.32(13) . . . . ?
C1 S1 N1 C8 -27.72(15) . . . . ?
O1 S1 C1 C2 -74.81(12) . . . . ?
N1 S1 C1 C2 57.11(12) . . . . ?
C9 S1 C1 C2 169.83(10) . . . . ?
S1 C1 C2 C3 -59.41(13) . . . . ?
S1 C1 C2 C15 175.89(10) . . . . ?
C15 C2 C3 C4 -25.2(2) . . . . ?
C1 C2 C3 C4 -147.08(14) . . . . ?
C15 C2 C3 C8 156.14(14) . . . . ?
C1 C2 C3 C8 34.30(18) . . . . ?
C8 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C4 C5 -178.98(14) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C3 -0.3(2) . . . . ?
C6 C7 C8 N1 179.97(15) . . . . ?
C4 C3 C8 C7 0.8(2) . . . . ?
C2 C3 C8 C7 179.52(14) . . . . ?
C4 C3 C8 N1 -179.51(15) . . . . ?
C2 C3 C8 N1 -0.8(2) . . . . ?
S1 N1 C8 C7 179.83(12) . . . . ?
S1 N1 C8 C3 0.2(2) . . . . ?
O1 S1 C9 C10 -11.33(16) . . . . ?
N1 S1 C9 C10 -141.27(14) . . . . ?
C1 S1 C9 C10 104.87(14) . . . . ?
O1 S1 C9 C14 167.87(13) . . . . ?
N1 S1 C9 C14 37.92(15) . . . . ?
C1 S1 C9 C14 -75.94(15) . . . . ?
C14 C9 C10 C11 -2.0(3) . . . . ?
S1 C9 C10 C11 177.14(14) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 C14 -2.3(3) . . . . ?
C12 C13 C14 C9 1.3(3) . . . . ?
C10 C9 C14 C13 0.9(3) . . . . ?
S1 C9 C14 C13 -178.31(13) . . . . ?
C3 C2 C15 C16 175.61(13) . . . . ?
C1 C2 C15 C16 -61.80(16) . . . . ?
C2 C15 C16 O2 -20.8(2) . . . . ?
C2 C15 C16 C17 159.78(14) . . . . ?
O2 C16 C17 C22 178.10(17) . . . . ?
C15 C16 C17 C22 -2.5(2) . . . . ?
O2 C16 C17 C18 -1.8(2) . . . . ?
C15 C16 C17 C18 177.59(16) . . . . ?
C22 C17 C18 C19 -0.9(3) . . . . ?
C16 C17 C18 C19 179.00(19) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 C21 0.9(4) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
C18 C17 C22 C21 1.1(3) . . . . ?
C16 C17 C22 C21 -178.83(19) . . . . ?
C20 C21 C22 C17 -0.3(4) . . . . ?
